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Complete all Cave flipper levels without dying.

This achievement unlocks upon obtaining the "First Run" medal on all of the Cave levels. To check your progress, from the map screen you can scroll over all of the cave levels to check if the green First Run medal is lit up next to the level.

The achievement description is confusing compared to the actual requirements. There is no way to finish the level while dying, but the "First Run" medal makes it seem as though you need to beat each Cave level on your first try or you miss the medal. Thankfully this isn't the case.

If you are attempting a Cave level and you die and respawn at the start of the level, you will not be able to unlock the First Run medal unless you quit out to the main menu, then choose Level Select and pick the level you were working on. Quitting out to the map screen isn't enough. The game will still "remember" you didn't do it first try. Because of this, I highly recommend using the following approach (and exploit).

Pausing the game and selecting Restart to restart a level does not count as a death. So if you die, quickly pause the game during the death animation and choose to Restart. This gives you unlimited tries at beating the Cave levels without dying and eliminates the hassle of continually quitting out to the main menu after every attempt.

With this approach in use, it really just becomes a matter of beating each Cave level to unlock this achievement. If you aren't quick enough to pause and restart, just quit out to the main menu then jump right back in.

Once you've got the green First Run medal on all Cave levels, the achievement will unlock.